The Ultimate Bermuda Cup Match Itinerary & Guide

Held every summer, the Bermudian tradition of Cup Match is much more than a crowning cricket competition. It honours Emancipation Day and Mary Prince Day, blending sport, history, and unmatched island energy. It’s a moment when the island lets loose with Crown & Anchor games, beach parties, team colours, and camps filled with food, friends, and laughter.

Whether you’re a first-timer or a regular visitor, this guide will help you experience Cup Match the Bermudian way – up close, and all in.

Where to Stay 

Where you stay during Cup Match can shape your entire experience. In odd-numbered years like 2025, the match is hosted by St. George’s Cricket Club on the East End – stay close to the action at spots like St. George’s Club or Hillcrest Boutique Hotel. In even-numbered years, the West End hosts the festivities, with top accommodations including Cambridge Beaches and The Reefs Resort & Club. 

Whether you’re steps from the cricket grounds or just a scenic ferry ride away, booking early is key – Cup Match is one of Bermuda’s busiest (and most beloved) weekends.  

A Day-by-Day Cup Match Itinerary

Tuesday

After arriving and settling in, ease into island time with a breezy beach break. You’re perfectly positioned to relax by the pool or explore some of Bermuda’s most beautiful stretches of sand, like the family-friendly Shelly Bay, the secluded coves of Clearwater and Turtle Bay, the snorkel-ready reefs at John Smith’s Bay, and the postcard-perfect waters of Tobacco Bay. Prefer something even more private? Seek out romantic Drew’s Bay. Soak up the serenity, because the next few days will be packed with cricket action and celebration. Tonight, rest up – Cup Match energy is just beginning to build!

Wednesday

Start your day with a deep dive into Bermuda’s rich history. Explore the UNESCO World Heritage site Town of St. George and tour local landmarks and museums, including the Bermuda Heritage Museum, home to powerful stories of emancipation and resilience. Then, it's time to choose your side: pick up your team colours – red and navy blue for Somerset, or light blue and navy blue for St. George’s. As evening falls, head to Hamilton for Harbour Nights, where the streets come alive with music, food, and island flair.

Thursday & Friday

It’s time for the main event – the two-day Cup Match Cricket Classic. Head to the cricket grounds for the legendary showdown between St. George’s and Somerset. Whether you're a cricket fan or not, the atmosphere is electric, with music, local food stalls, the lively Crown and Anchor tent, and team spirit all around. Dress the part with bold team colours, stylish flair, and sun-smart essentials. Want the best seat in the house? Purchase a game ticket for $25, and then head to Camp Bermuda – a free, fun-filled hospitality area designed for visitors looking to experience the Cup Match spirit like a local. 

Cup Match fun isn’t limited to the field. On Thursday, join locals at Horseshoe Bay to celebrate Day 1 with beach vibes and ocean dips, or rent a boat and cruise to Paradise Lakes for a floating concert by the Go Down Berries – yes, the band performs from a boat! On Friday, hop aboard the Ubervida's Special Cup Match Mini Cruise from Hamilton to St. George’s for a festive ride. Prefer a laid-back scene? Head to Admiralty House Park, Spanish Point Park, or Warwick Long Bay, where locals camp, cook out, and enjoy the long weekend.

Saturday

After two high-energy days, Saturday is your time to recharge. Start slow – sleep in, stroll the beach, or simply relax with a leisurely breakfast. Once you’ve refuelled, head into Hamilton for a relaxed afternoon of culture and cuisine. Enjoy lunch at a harbourside café, then wander the Bermuda National Gallery, take a tour of murals and street art, and shop eclectic boutiques. From bold contemporary art to handcrafted jewellery, the city’s creative scene offers the perfect blend of inspiration and island charm.

Sunday

Wrap up your Cup Match weekend with Non-Mariners Day. What started as a race of intentionally doomed vessels has evolved into Bermuda’s biggest raft-up party. Head to Mangrove Bay in Sandys Parish, where boats of all shapes and sizes drop anchor for a full day of music, dancing, and pure fun on the water. Rent your own boat or book a spot on a party yacht like ÜberVida for prime views, an open bar, and DJs spinning all day. It’s the perfect splashy send-off to an epic weekend.

Evening Events & Parties During Cup Match

While the cricket match is the heart of Cup Match, the real magic happens all around it – especially after dark. The island lights up with music, dancing, and high-energy events that make the long weekend unforgettable.

Kick things off on Cup Match Eve, Wednesday, July 30, with reggae royalty Tarrus Riley performing live at the National Sports Center. His soulful hits, like “She’s Royal,” set the perfect tone for an island night under the stars. VIP tickets come with parking, drinks, buffet, and front-stage access.

On Thursday, July 31, soca fans take over at Wet Fete '25: Enter the Jungle, held at Snorkel Park Beach. Expect non-stop energy, beach vibes, and a killer DJ lineup starting at 9 p.m.
Friday, August 1 brings back the legendary Soca vs. Reggae showdown at Tiger Bay. It’s the return of a fan-favourite, packed with epic DJ battles and live performances by V’ghn for Team Soca and Cham for Team Reggae. Doors open at 8:30 p.m. – don’t miss it.

Finally, on Saturday, August 2, things get wild at the Bacchanal Run – Bermuda’s vibrant paint, powder, and water truck road party. It’s messy, it’s joyous, and it’s pure Cup Match fun.

Dining During Cup Match

Cup Match is the perfect time to celebrate Bermuda’s bold flavours and beloved traditions. From sizzling food stalls at the cricket grounds to seaside restaurants embracing the holiday spirit, this is the weekend to taste your way through the island. 

Classic Bermudian dishes take centre stage: savour curried mussel pie with its signature dollop of mayo, rich fish chowder spiked with Sherry Peppers and Black Seal Rum, crispy conch fritters with mustard mayo, and the ever-popular Bailey’s Bay fish sandwich, piled high with battered fish, cheese, tomato, and tartar sauce.

You’ll also find fish cakes tucked into hot cross buns, cassava pie, peas and rice, fall-off-the-bone BBQ ribs, shark hash, and coconut cake – all part of the Cup Match flavour parade.

For sit-down meals, the East End delivers with the iconic Swizzle Inn (for a classic Rum Swizzle and pub fare), ocean-fresh seafood at Wahoo’s Bistro, scenic views at Achilles Restaurant or casual bites from Munchies By the Sea.

If you’re celebrating from the West End, the Frog & Onion Pub, located in the historic Royal Naval Dockyard, serves hearty British-Bermudian fare in a lively setting. For something more upscale, reserve a table at Breezes for a romantic oceanfront dinner, or indulge in fine dining at The Waterlot, one of Bermuda’s most iconic steak and seafood restaurants.

Wherever you dine, expect warm hospitality and a celebratory spirit. Pro Tip: book early – tables fill fast.

Tips for Getting Around

Getting around during Cup Match weekend takes a little planning, but it’s all part of the adventure. Bermuda’s buses and ferries are reliable, but keep in mind that public transport runs on limited schedules during the Thursday and Friday public holidays. Be sure to buy your tokens or transportation passes in advance, and check routes carefully – some may be delayed or rerouted near Cup Match venues.

Taxis are available but in high demand, especially around match times and evening events. Booking early is key. Alternatively, Hitch and Bermuda Island Taxi offers a convenient and cashless way to get where you're going.

For maximum flexibility, consider renting a scooter or electric microcar. These are perfect for beach hopping, exploring camping zones, and finding those off-the-beaten-path gems. Just remember: roads are narrow, we drive on the left, and drinking and driving is a no-go.

Explore more ways to get around Bermuda. And remember – whether you're headed to the cricket grounds or the beach, a little preparation goes a long way in keeping your Cup Match experience smooth and stress-free.

Come for the Cricket, Stay for the Culture

More than a holiday, Cup Match is a vibrant fusion of sport, history, and celebration that captures the heart of Bermuda. From the roar of the crowd to the rhythm of beachside concerts, every moment invites you deeper into the island’s culture. And once you’ve experienced it – cheered a team, shared a swizzle, joined the fun – you’re not just a visitor anymore. You’re part of the island family.